Hitting six figures within three months of launching an AI bootcamp

Ben Issen built a portfolio of tools, sold eight of them, and used the money to fund his online school teaching practical AI skills.

A few months after launch, Side School has already brought in over six figures.

Here's Ben on how he did it. 👇

Selling eight products

I’m the son of an entrepreneur and designer, so I grew up building tons of small projects and filming them. At 18, I became Webflow’s first intern, and that made me want to build tools for creatives. Which I did. =

Right after university, I started a personal incubator called Supercreative that built tools for freelance designers. I designed, coded, and marketed over 18 tools, some with the help of developers with whom I split profits. After four years, I sold eight of these tools to acquirers on Twitter and acquire.com, and moved on to build a school for adults. 

So, I’m now the co-founder of Side School, where we teach practical AI skills with challenge-based learning. Our bootcamps are designed to solve real-world problems, making the learning process both engaging and industry-relevant.

We launched a few months ago and Side School has already generated six figures in revenue in our initial experiments. Now, we’re focusing on scaling the business.

Starting a school

The idea for Side School stemmed from my frustration with traditional education models. I wanted to create a better way to learn by doing — solving challenges inspired by real-world scenarios.

Selling Supercreative gave me enough runway to experiment with novel ideas for a few years. But instead of exploring alone, I wanted a team. I made a list of potential cofounders who matched the criteria I had set, and met with all of them. Zineb Salamat, who previously launched six online schools, had the experience and energy I was looking for. She was looking for someone like me too. As we started working together, we knew the success of the company would rely on our mutual support. We’re a great duo. 

After four weeks of working together, we launched the first bootcamp: “AI for Designers”. It grouped many intuitions that we had. Validation then came from seeing our first bootcamp participants gain confidence and achieve measurable results using AI.

Some even said the overall experience was life-changing, so we knew we were on the right path. 

Lean building

With me funding the project, time was our major constraint. We wanted validation fast. So, building Side School was a lean process.

It took four weeks to design and launch the first challenge-based bootcamp. I used tools like ChatGPT, Framer, Discord, Whimsical, and Figma to create a no-code MVP, ensuring I could test the concept without heavy upfront investments.

Beyond that, we used Notion for course management, Tally for collecting feedback, and Whereby for live sessions. Over time, we’ve started integrating Customer.io for the platform, and exploring tools like Google Tag Manager for tracking conversions. We built our own platform (our LMS) with Supabase and we enjoy Motor Admin for simplifying ops tasks. 

We get feedback on almost every decision we make with our AI coach, a GPT we built, that has all the context on what we work on.

Using Krea, V7 Go, and Lindy have also been extremely useful for us to go super fast. These are the types of AI tools that feel to me like the hidden gem Webflow was back in 2015. 

Growing the model

We started generating revenue in the first month of existence, which was important to us. We needed to understand whether there was real interest in what we offered. 

Our one-month bootcamps cost $1400 per person, charged once. And we'll be increasing pricing soon.

We’re getting close to 350 students. We’re focusing mostly on the French market, and expanding slowly to Europe and North America with English-speaking bootcamps. 

We also have an offer to organize internal bootcamps for medium and large companies. And we’re exploring selling subscription seats to enterprises.

Sales-driven growth

One of the biggest challenges has been identifying the right distribution channels. Early on, I tried multiple approaches — cold outreach, social media campaigns, and partnerships — but none yielded consistent results. This taught me the importance of structured experimentation.

We started growing organically from word of mouth and leveraging my network of freelancers from Supercreative. Since then, social media posts highlighting success stories and case studies have also helped build credibility.

But the majority of our growth comes from sales. I’m very used to product-driven growth, so this was new to me, but it's very important when you average deal size is about $3k. We have two sales people doing outreach via LinkedIn. And when we get an SMB as a client, they onboard multiple employees at a time — sometimes dozens of employees at once. 

Beyond that, a pivotal moment was organizing free challenges where participants could test their skills before joining the bootcamp. This approach not only generated interest but also showcased the value of Side School’s methodology.

Refining the offer and clarifying the messaging were important factors too. For example, we switched from saying “action training” to saying “bootcamps” instead. 

The hyper-freelance model

Five years ago, I wrote this article on Indie Hackers called the Hyper Freelance Model. Starting with freelancing to build skills, then sharing what you know, then building personal projects, seems to be a great way to start out.

And if you'd like some resources, here are some books that we found helpful:

• Founding Sales

• Disciplined Entrepreneurship

On a personal note, I love the essay “How to do Great Work”.

What's next?

I want to keep thinking about this question that I’ve been continuously fascinated by: How do we create better systems to learn online?

We'll keep playing with the building blocks we started with: Bootcamps, challenges, AI, etc. With our small team and limited resources, I think we can be super creative in finding novel ways to make online learning better. 

You can follow along on X, LinkedIn. And check out Side School.